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Nucleophilic addition of bulk chemicals with imines using N-functionalized hydroxylamine reagents as precursors

Author

Listed:
  • Wei Wang

    (Central China Normal University (CCNU)
    Wuhan Institute of Technology)

  • Yuanyuan Peng

    (Wuhan Institute of Technology)

  • Yang Liu

    (Central China Normal University (CCNU)
    Wuhan Institute of Technology)

  • Yanchun Lin

    (Wuhan Institute of Technology)

  • Fei Zhao

    (Wuhan Institute of Technology)

  • Qinlin Chen

    (Central China Normal University (CCNU)
    Wuhan Institute of Technology)

  • Liangming Xuan

    (Wuhan Institute of Technology)

  • Qiongjiao Yan

    (Wuhan Institute of Technology)

  • Fen-Er Chen

    (Fudan University)

  • Hui Zhou

    (Central China Normal University (CCNU)
    China West Normal University)

Abstract

C–C and C–X bond forming reactions are essential tools in organic synthesis, constantly revolutionizing human life. Among the key methods for constructing new chemical bonds are nucleophilic addition reactions involving imines. However, the inherent challenges in synthesizing and storing imines have stimulated interest in designing stable precursors, which generates imines in situ during the reaction. This approach offers a promising alternative to traditional strategies and holds significant potential for future applications. Here we report a direct and general nucleophilic addition of imines with cost-effective feedstocks and easily accessible nucleophiles, specifically utilizing N‑functionalized hydroxylamine reagents as bench-stable precursors. This methodology streamlines the synthesis of various products, such as amino acid derivatives, through a wide range of reaction types, including C–C, C–N, C–O, and C–S bond constructions. Mechanistic studies and DFT calculations provide insights into a plausible reaction mechanism that supports the in-situ imine formation.

Suggested Citation

  • Wei Wang & Yuanyuan Peng & Yang Liu & Yanchun Lin & Fei Zhao & Qinlin Chen & Liangming Xuan & Qiongjiao Yan & Fen-Er Chen & Hui Zhou, 2025. "Nucleophilic addition of bulk chemicals with imines using N-functionalized hydroxylamine reagents as precursors," Nature Communications, Nature, vol. 16(1), pages 1-12, December.
    • Handle: RePEc:nat:natcom:v:16:y:2025:i:1:d:10.1038_s41467-024-55488-0
    DOI: 10.1038/s41467-024-55488-0
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    References listed on IDEAS

    as
    1. Yingcheng Wang & Mingjie Mo & Kongxi Zhu & Chao Zheng & Hongbin Zhang & Wei Wang & Zhihui Shao, 2015. "Asymmetric synthesis of syn-propargylamines and unsaturated β-amino acids under Brønsted base catalysis," Nature Communications, Nature, vol. 6(1), pages 1-9, December.
    2. Jung Woon Yang & Carley Chandler & Michael Stadler & Daniela Kampen & Benjamin List, 2008. "Proline-catalysed Mannich reactions of acetaldehyde," Nature, Nature, vol. 452(7186), pages 453-455, March.
    3. Yingcheng Wang & Sheng Wang & Wenyu Shan & Zhihui Shao, 2020. "Direct asymmetric N-propargylation of indoles and carbazoles catalyzed by lithium SPINOL phosphate," Nature Communications, Nature, vol. 11(1), pages 1-10, December.
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